Iodine → 3-Iodo-5-phenylsulfanyl-1H-pyrrolo[2,3-b]pyridine

HRID 1991094노트

반응식

HRID 1991094 반응식
[C:1]1([S:7][C:8]2[CH:9]=[C:10]3[CH:16]=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[I:19]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C.O>[I:19][C:16]1[C:10]2[C:11](=[N:12][CH:13]=[C:8]([S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:9]=2)[NH:14][CH:15]=1

참가 물질

7

반응물 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 591287095-Phenylsulfanyl-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 591287053-Iodo-5-phenylsulfanyl-1H-pyrrolo[2,3-b]pyridine수율 98%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2 (135 mg, 0.60 mmol) in DMF (1.5 mL) was added solid KOH (124 mg, 2.21 mmol) and the reaction mixture stirred for 20 min. Iodine (167 mg, 0.66 mmol) was then added and the stirring continued for 40 min. A mixture of water (8.8 mL) and sat. aq. Na2S2O3 (1.3 mL) was added rapidly, and the resulting solid filtered off, washed with water (2×) and dried in vacuum to give iodide 3 as a creamy solid (205 mg, 98%); 1H NMR (400 MHz, CDCl3+2 drops CD3OD) δ 7.10-7.30 (m, 5H), 7.45 (s, 1H), 7.94 (d, J=2.0 Hz, 1H), 8.35 (d, J=1.9 Hz, 1H).

후처리

  1. waitthe stirring continued for 40 min
  2. additionwas added rapidly
  3. filtrationthe resulting solid filtered off
  4. washwashed with water (2×)
  5. customdried in vacuum

출처 및 근거

ORD 기록
ord-333e844165204f2bb43227c41999f2f3
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645769B2

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